Top Maine Cruises & Sailing - page 2

Explore the highlights of Maine's Acadia National Park during this private, half-day guided tour. Get personalized recommendations and information from your tour guide. Cover the Park Loop Road, with panoramic views from Cadillac Mountain—no climbing necessary. Tours include private transfers in a climate-controlled vehicle.

Discover the wonders of Acadia with all the sights included in the Sea to Summit tour plus the chance to see so much more of Mount Desert Island! After descending Cadillac Mountain we will head to the one-of-a-kind Somes Sound. We will see more stone bridges, lakes, ponds, streams, cliffs, beaches and coves along the way. You’ll be inspired by the beauty of the Tarn, Hadlock Pond, Eagle Lake, Seal Harbor Beach, Little Long Pond, and the majestic vistas off the cliffs of Cooksey Drive where the rich and famous dwell. You’ll have the opportunity to enjoy the beauty and serenity of Thuya Gardens, and/or Asticou Gardens, before driving the full length of Somes Sound by way of Northeast Harbor. No watching the clock here, we give you extra time to enjoy your day! Expect your tour guide to be dependable, friendly, and adaptable. We care about your experience on Mount Desert Island! Sit back and expect your guide to know exactly where you want to go and what you want to see.

An excellent tour is so much more than a checklist of stops or stories. We will create a meaningful experience you'll cherish as we explore Acadia and the many hidden gems just outside of the national park on a half-day adventure tailored specifically to your group. No rush, no crowded bus. Just you, riding in comfort with guides who never tire of sharing our island. We'll handle the passes and driving, leaving you free to really enjoy Acadia. We know the secrets to escaping the press of crowded areas, while ensuring you don't miss a thing. Our guides thrive on adjusting tours to match your group's interests and abilities. A great tour leaves you brim-full of the magic of this lovely place. Sure, there are stories, tour guide puns, pictures to take, history and trivia you might forget.. but mainly, that feeling of really experiencing this place in a special way. You will leave, knowing you saw and felt more, with less stress, than anyone choosing to explore without a local expert.

See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.

Make the most of your visit to Maine's Acadia National Park during this private, 3-hour guided tour. Discover top highlights and hidden gems along the Park Loop Road, Otter Cliffs, Thunder Hole, Sand Beach, and more, and enjoy panoramic views from Cadillac Mountain. Tours include bottled water, snacks, entrance fees, and private transfers in a climate-controlled vehicle.

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation or renting a car on this small-group guided tour of Portland's must-see sights. Stop in downtown Portland and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Known for its rocky coastlines, wealth of wildlife, and evergreen forests, Acadia National Park promises dramatic scenery—and this fully narrated driving tour makes for an easy way to discover it. Set off from Bar Harbor in a luxury Berkshire minibus, and discover highlights like Cadillac Mountain (the highest point on the East Coast), Thunder Hole (where ocean waves roar), Sieur De Mont's Spring, Jordan Pond, and much more.

Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.

Wonder at the views from atop of the highest mountain on the eastern seaboard of the United States. From the shore of Sand Beach to the peak of Cadillac Mountain you’ll have the chance to explore the whole 27 miles (43 km) of Acadia’s Park Loop Road. As we meander along shores, coves, cliffs, historic stone bridges, through the woods, and up the mountain, your guide will introduce you to local history, lore, flora, fauna, and geology. You’ll have the opportunity to stop for photos and/or get out to explore as you wish. Sights will included the Wild Gardens of Acadia, Sand Beach, Thunder Hole, Otter Cliffs, Hunters Beach, Jordan Pond, Bubble Pond, Eagle Lake, and Cadillac Mountain Summit. We reserve an extra 30 minutes on every tour so you can relax and not have to watch the clock! Expect your tour guide to be dependable, friendly, and adaptable. We care about your experience on Mount Desert Island! Expect your guide to be knowledgeable and passionate about the Island.

Discover top sights within Acadia National Park on this 6-hour private tour with your own guide. Cover more locations in less time in a comfortable, air-conditioned vehicle. Highlights include the Park Loop Road, panoramic views from Cadillac Mountain, a stroll through Asticou Gardens, and a lobster lunch stop in Southwest Harbor (meal not included).

Acadia National Park is as big as it is beautiful, making it simple to get lost when going on your own. Instead, choose this self-guided driving audio tour and see the park’s pristine wilderness while hearing about its history from the safety of your own vehicle. Follow a route through the park on an easy-to-download app that gives recommended speed limits and commentary for a unique experience.

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you to soak in the stunning scenery while learning about the rich history of the area, including the iconic Wood Island Lighthouse and Biddeford Pool. Perfect for all ages, this charter offers a relaxing atmosphere where you can create lasting memories with family and friends amidst the beautiful Maine coastline. Alternative Biddeford Pickup - From Kennebunkport area this location will save 40 minutes of driving.

All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests.

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designer, John Alden. Heart's Desire measures 53' feet and features some of John Alden's trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine.

Acadia's autumn paints a vibrant scene with fiery hues of red, gold, and russet, reflecting on the calm waters and pink granite cliffs of the Acadia National Park. The air turns crisp, carrying the scent of pine and the whisper of falling leaves. It's a season of beauty and tranquility, a time to witness the wildness of nature transforming into a spectacle of color before the quiet of winter.

100% Private Charter for Groups up to 16 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate experience on Casco Bay. Unlike crowded public cruises, your group of up to 15 guests will enjoy the full comfort and charm of one of our classic wooden vessels—all to yourselves. Cruise past iconic lighthouses, historic granite forts, and stunning stretches of Maine’s coastline, with opportunities to spot harbor seals, seabirds, and other local wildlife along the way. Whether you’re celebrating a special occasion or simply gathering with friends, this charter offers a personalized, relaxed way to experience the best of coastal Maine. Feel free to bring your own food—we provide all the glassware, plates, and utensils you’ll need. Local craft beer, wine, and other beverages are also available for purchase onboard. Due to our liquor license, we do NOT permit outside alcoholic beverages on board.

Join us on a fall adventure to explore Downeast Maine at its peak beauty. This tour will take visitors to hidden small gems to connect with the beautiful coast of Maine and see how locals live here. Your local guide will drive you on a 4 hour ride leaving from Mount Desert Island stopping frequently for sweeping views and bountiful opportunities for pictures. After getting out on coastal Route 1, we will stop at some lookout points to catch glimpses of Bar Harbor from afar. Stopping in MIlbridge for unique ocean views, Cherryfield for the river, and finally head into the hills of Blackswoods for lake and mountain views. Cell service is limited in the Blackswoods Rd. Pickup can be arranged at any local hotel or rental within MDI. Alternatively free parking and pickup is available at the Gateway Visitors Center in Trenton. Your local guide will make sure get the best views of while sharing information about wildlife, landmarks, and what it's like to live in Maine.

This tour includes everything that the "Sea to Summit" and the "Wonders of Acadia" tours have to offer. Then we’ll continue on our journey to the picturesque village of Somesville, and scenic Southwest Harbor. We’ll see Echo Lake, the natural Seawall, and perhaps take the time to explore the oceanside Wonderland Trail. Then we will move on to the iconic Bass Harbor Lighthouse. Start your tour predawn to witness the first sunrise in the USA from Cadillac Mountain Summit!

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.

Discover the captivating history of Bar Harbor, Maine, once the summer playground of America’s elite. This self-guided walking tour unveils the rise and fall of this glamorous resort town, where the Vanderbilts and Rockefellers built grand estates along the rugged coastline. With GPS-triggered narration, stroll from Agamont Park to the iconic Bar Island Land Bridge, exploring historic sites, stunning architecture, and hidden stories shaped by both opulence and tragedy. - Self-guided audio tour with GPS navigation for flexibility - Duration of approximately 60–120 minutes—explore at your own pace - Visit landmarks like the Bar Harbor Inn and La Rochelle Mansion - No internet needed; download and go offline for convenience

There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. Every sailing day trip in Maine we offer is fully customizable and built around your group’s vision of a perfect day on the water. Whether we’re exploring the islands, sailing past lighthouses, or anchoring at a secluded cove for a swim, the goal is simple: give you a day that feels easy, personal, and genuinely fun.

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboard our vessel, where every moment unfolds as a cherished tale. Explore the hidden wonders of the Saco River and Saco Bay under the guidance of our seasoned crew. Surrender to the serene embrace of the moment as the ocean murmurs its secrets and the sun paints the horizon with a radiant glow. Seize the opportunity to take the helm and experience the exhilaration of sailing firsthand. Whether craving adventure or seeking inner peace, our private sunset sail promises an unparalleled experience. Allow us to craft an unforgettable journey that lingers in your heart long after the sun has dipped below the horizon. Alternative pickup available in Biddeford for added cost, saves 40 min of driving, contact us for availability.